A Continuous-Flow Cascade Reactor System for Subtilisin A- Catalyzed Dynamic Kinetic Resolution of N-tert-Butyloxycarbonylphenylalanine Ethyl Thioester with Benzylamine

Advanced Synthesis and Catalysis

Volumn 358, Issue 10, 2016, Pages 1608-1617

  Falus, Péter ^a   Cerioli, Lorenzo ^b   Bajnóczi, Gabriella ^a   Boros, Zoltán ^a,c   Weiser, Diána ^a   Nagy, József ^a,c   Tessaro, Davide ^b,d   Servi, Stefano ^b,d   Poppe, László ^a,c  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b POLITECNICO DI MILANO   (Italy)

^c SynBiocat Ltd   (Hungary)

^d UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

amino acid amides; biocatalysis; continuous flow biotransformation; dynamic kinetic resolution; enantioselectivity; subtilisin A; supported catalysts

Indexed keywords

EID: 84964329526     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201500902     Document Type: Article

References (78)

1. C. A. G. N. Montalbetti, V. Falque, Tetrahedron 2005, 61, 10827–10852.
2. T. Henkel, R. M. Brunne, H. Müller, F. Reichel, Angew. Chem. 1999, 111, 688–691;
3. Angew. Chem. Int. Ed. 1999, 38, 643–647;
4. A. K. Ghose, V. N. Viswanadhan, J. J. Wendoloski, J. Comb. Chem. 1999, 1, 55–68.
5. T. C. Nugent, (Ed.), Chiral Amine Synthesis, Wiley-VCH, Weinheim, 2010.
6. F. Albericio, R. Chinchilla, D. J. Dodsworth, C. Najera, Org. Prep. Proced. Int. 2001, 33, 203–303.
7. V. R. Pattabiraman, J. W. Bode, Nature 2011, 480, 471–479.
8. S. Kato, T. Murai, The Chemistry of Acid Derivatives, Vol. 2, (Ed.: S. Patai), Wiley, Chichester, 1992, pp 803–847.
9. F. Fécourt, B. Delpech, O. Melnyk, D. Crich, Org. Lett 2013, 15, 3758–3761.
10. D. Tessaro, L. Cerioli, S. Servi, F. Viani, P. D′Arrigo, Adv. Synth. Catal. 2011, 353, 2333–2338.
11. M. Caussette, A. Marty, D. Combes, J. Chem. Technol. Biotechnol. 1997, 68, 257–262.
12. A. Zaks, A. M. Klibanov, Proc. Natl. Acad. Sci. USA 1985, 82, 3192–3196.
13. K. C. Sproull, G. T. Bowman, G. Carta, J. L. Gainer, Biotechnol. Prog. 1997, 13, 71–76.
14. D. Bianchi, P. Cesti, J. Org. Chem. 1990, 55, 5657–5659.
15. H. Frykman, N. Ohrner, T. Norin, K. Hult, Tetrahedron Lett. 1993, 34, 1367–1370.
16. S. Iriuchijima, N. Kojima, J. Chem. Soc. Chem. Commun. 1981, 185–185.
17. K. Ding, Y. Uozumi, Handbook of Asymmetric Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2008.
18. L. Poppe, L. Novák, Selective Biocatalysis: A Synthetic Approach, Wiley-VCH, Weinheim, 1992.
19. nd edn., (Eds.: A. Liese, K. Seelbach, C. Wandrey), Wiley-VCH, Weinheim, 2006.
20. th edn., Springer, Berlin, Heidelberg, 2011.
21. Z. Boros, G. Hornyánszky, J. Nagy, L. Poppe, Stereoselective hydrolase-catalyzed processes in continuous-flow mode, in: Cascade Biocatalysis: Stereoselective and Environmentally Friendly Reactions, (Eds.: S. Riva, W. Fessner), Wiley-VCH, Weinheim, 2014.
22. U. T. Bornscheuer, R. J. Kazlauskas, Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, Wiley-VCH, Weinheim, New York, 2006.
23. A. Schmid, J. S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, B. Witholt, Nature 2001, 409, 258–268.
24. Practical Methods for Biocatalysis and Biotransformations, (Eds.: J. Whittal, P. Sutton), John Wiley & Sons, Ltd., Chichester, 2010.
25. Green Chemistry in the Pharmaceutical Industry, (Eds.: P. J. Dunn, A. S. Wells, M. T. Williams), Wiley-VCH, Weinheim, 2010.
26. E. Busto, V. Gotor-Fernández, V. Gotor, Chem. Soc. Rev. 2010, 39, 4504–4523.
27. M. S. Humble, P. Berglund, Eur. J. Org. Chem. 2011, 3391–3401.
28. Z. Zhou, M. Hartmann, Top. Catal. 2012, 55, 1081–1100.
29. R. A. Sheldon, Adv. Synth. Catal. 2007, 349, 1289–1307.
30. C. Mateo, J. M. Palomo, G. Fernandez-Lorente, J. M. Guisan, R. Fernandez-Lafuente, Enzyme Microb. Technol. 2007, 40, 1451–1463.
31. U. Hanefeld, L. Gardossi, E. Magner, Chem. Soc. Rev. 2009, 38, 453–468.
32. C. Garcia-Galan, A. Berenguer-Murcia, R. Fernandez-Lafuente, R. C. Rodrigues, Adv. Synth. Catal. 2011, 353, 2885–2904.
33. R. A. Sheldon, S. van Pelt, Chem. Soc. Rev. 2013, 42, 6223–6235.
34. R. C. Rodrigues, C. Ortiz, A. Berenguer-Murcia, R. Torres, R. Fernández-Lafuente, Chem. Soc. Rev. 2013, 42, 6290–6307.
35. A. Woschek, W. Lindner, F. Hammerschmidt, Adv. Synth. Catal. 2003, 345, 1287–1298.
36. J. Holt, I. W. C. E. Arends, A. J. Minnaard, U. Hanefeld, Adv. Synth. Catal. 2007, 349, 1341–1344.
37. D. Arosio, A. Caligiuri, P. D′Arrigo, G. Pedrocchi-Fantoni, C. Rossi, C. Saraceno, S. Servi, D. Tessaro, Adv. Synth. Catal. 2007, 349, 1345–1348.
38. G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708–5723.
39. S. Ceylan, A. Kirschning, in: Recoverable and Recyclable Catalysts, (Ed.: M. Benaglia), John Wiley & Sons, New York, 2009, pp 379–410.
40. X. Y. Mak, P. Laurino, P. H. Seeberger, Beilstein J. Org. Chem. 2009, 5, 19.
41. M. Rasheed, S. C. Elmore, T. Wirth, in: Catalytic Methods in Asymmetric Synthesis – Advanced Materials, Techniques, and Applications, (Eds.: M. Gruttadauria, F. Giacalone), John Wiley & Sons, Hoboken, 2011, pp 345–372.
42. R. Yuryev, S. Strompen, A. Liese, Beilstein J. Org. Chem. 2011, 7, 1449–1467.
43. nd edn., (Ed.: T. Wirth), Wiley-VCH, Weinheim, 2013.
44. P. Falus, Z. Boros, P. Kovács, L. Poppe, J. Nagy, J. Flow Chem. 2014, 4, 125–134.
45. M. Miyazaki, H. Maeda, Trends Biotechnol. 2006, 24, 463–470.
46. K. Kawakami, D. Abe, T. Urakawa, A. Kawashima, Y. Oda, R. Takahashi, S. Sakai, J. Sep. Sci. 2007, 30, 3077–3084.
47. T. Honda, M. Miyazaki, Y. Yamaguchi, H. Nakamura, H. Maeda, Lab Chip 2007, 7, 366–372.
48. Z. Wang, X. Li, W. Wang, Y. Tang, Y. Zhang, J. Catal. 2013, 300, 1–8.
49. C. Csajági, G. Szatzker, E. R. Tőke, L. Ürge, F. Darvas, L. Poppe, Tetrahedron: Asymmetry 2008, 19, 237–246.
50. G. Hellner, Z. Boros, A. Tomin, L. Poppe, Adv. Synth. Catal. 2011, 353, 2481–2491;
51. Z. Boros, P. Falus, M. Márkus, D. Weiser, M. Oláh, G. Hornyánszky, J. Nagy, L. Poppe, J. Mol. Catal. B 2013, 85–86, 119–125;
52. Z. Boros, D. Weiser, M. Márkus, E. Abaháziová, Á. Magyar, A. Tomin, B. Koczka, P. Kovács, L. Poppe, Proc. Biochem. 2013, 48, 1039–1047.
53. A. Kamal, M. A. Azhar, T. Krishnaji, M. S. Malik, S. Azeeza, Coord. Chem. Rev. 2008, 252, 569–592.
54. R. Marcos, B. M. Martín-Matute, Isr. J. Chem. 2012, 52, 639–652.
55. K. P. J. Gustafson, R. Lhammar, O. Verho, K. Engström, J.-E. Bäckvall, J. Org. Chem. 2014, 79, 3747–3751.
56. H. Pellissier, Tetrahedron 2008, 64, 1563–1601.
57. Y. Ahn, S-B. Ko, M.-J. Kim, J. Park, Coord. Chem. Rev. 2008, 252, 647–658.
58. B. Martín-Matute, J.-E. Bäckvall, Curr. Opin. Chem. Biol 2007, 11, 226–232.
59. A. S. de Miranda, L. S. M. Miranda, R. O. M. A. de Souza, Biotechnol. Adv. 2015, 33, 372–393.
60. S. J. Connon, Synlett 2009, 3, 354–376.
61. S.-K. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621–631.
62. P. Lozano, T. De Diego, S. Gmouh, M. Vaultier, J. L. Iborra, Int. J. Chem. React. Eng. 2007, 5, article A53.
63. P. Lozano, T. De Diego, M. Larnicol, M. Vaultier, J. L. Iborra, Biotechnol. Lett. 2006, 28, 1559–1565.
64. P. Lozano, T. De Diego, C. Mira, K. Montague, M. Vaultier. J. L. Iborra, Green Chem. 2009, 11, 538–542.
65. P. Lozano, T. De Diego, M. Vaultier, J. L. Iborra, Int. J. Chem. React. Eng. 2009, 7, article A79.
66. H. Pellissier, Tetrahedron 2011, 67, 3769–3802.
67. N. Itoh, M. Nakamura, K. Inoue, Y. Makino, Appl. Microbiol. Biotechnol. 2007, 75, 1249–1256.
68. M. D. Truppo, D. J. Pollard, J. C. Moore, P. N. Devine, Chem. Eng. Sci. 2008, 63, 122–130.
69. A. S. de Miranda, R. O. M. A. de Souza, L. S. M. Miranda, RSC Adv. 2014, 4, 13620–13625.
70. C. Roengpithya, D. A. Patterson, A. G. Livingston, P. C. Taylor, J. L. Irwin, M. R. Parrett, Chem. Commun. 2007, 3462–3463.
71. L. Poppe, A. Tomin, Z. Boros, E. Varga, L. Ürge, F. Darvas, Novel method for dynamic kinetic resolution (Új dinamikus kinetikus reszolválási eljárás), Hungarian Patent Application, P0900720, 2009.
72. Z. Wang, X. Li, W. Wang, Y. Tang, Y. Zhang, J. Catal. 2013, 300, 1–8.
73. L. N. Corîci, A. E. Frissen, D. J. van Zoelen, I. F. Eggen, F. Peter, C. M. Davidescu, C. G. Boeriu, J. Mol. Catal. B 2011, 73, 90–97.
74. Y.-F. Wang, K. Yakovlevsky, N. Khalaf, B. Zhang, A. L. Margolin, Ann. N. Y. Acad. Sci. 1996, 799, 777–783;
75. Y.-F. Wang, K. Yakovlevsky, B. Zhang, A. L. Margolin, J. Org. Chem. 1997, 62, 3488–3495.
76. P. J. Ganz, M. D. Bauer, Y. Sun, A. M. Fieno, R. A. Grant, P. E. Correa, M. Laskowski, C. W. Saunders, Protein Eng. Des. Sel. 2004, 17, 333–339.
77. P. D′Arrigo, D. Arosio, L. Cerioli, D. Moscatelli, S. Servi, F. Viani, D. Tessaro, Tetrahedron: Asymmetry 2011, 22, 851–856.
78. Y-C. Xie, H-Z. Liu, J-Y. Chen, Biotechnol. Lett. 1998, 20, 455–458.